Writer and speaker on culture, politics and spirituality. Works with arts and cultural organizations, funders, policymakers and educational institutions. Latest book: New Creative Community: The Art of Cultural Development.

Compassion: Annals of Online Dating

When packing for online dating world, be sure to bring along plenty of compassion.

Having chronicled my adventures in online dating in this blog series, I’ve become an object of curiosity to certain readers. They are waiting for my positive orientation toward this curious enterprise to cool off. “Are you still enjoying it?” they ask, and I can see that they don’t entirely believe it when I answer “Yes.”

I understand, of course. The enjoyment is akin to other pleasures that require a certain level of preparation and determination. Maybe it’s analogous to running or weight-lifting: it definitely helps if you are willing to play through a bearable level of pain, because your playing field is the human heart, and the potential for injury is great.

But how you hold it helps a lot. The women who dislike online dating—and they are legion—often see it as a referendum on their worth, which is, of course, how women of my generation were trained to see dating in general. They recount the insults and disappointments they’ve experienced, and with straight women, the bottom line, as so often in our grand narrative of romance, is a litany of the other gender’s deficiencies. Men!

I’ve mostly avoided this by seeing it in what seems to me a more sensible light: as something like an elimination process, where I expect to meet a great many perfectly nice and kind men before encountering the one whose heart sings in time with my own. Along the way, I’m liberated by understanding that I don’t have to pay the slightest bit of attention to the directives I absorbed in my teen years. It isn’t my job to make the man like me, but to learn if we like each other; it’s about mystery and compatibility and luck, not worth. You show up as yourself, hoping your date does the same, and at the very least, you’ve encountered another human being and learned something.

The general outlines of online dating are simple: you make contact via a website, responding to each other’s photographs, self-description, vital statistics, and email communication. You arrange to meet for a walk, a coffee, a glass of wine, and from there, you either agree to meet again or shake hands and wish each other luck. The charm is that it gives you permission to skip over some of the more banal aspects of getting acquainted. If it quickly becomes clear that a deep connection will not be possible, you might resort to small talk to play out the time it takes to finish whatever you are drinking. But almost always, there is tacit permission to talk about things that matter, which makes online dating a kind of perfected version of all social intercourse: face each other, see who’s home, exchange truths, keep your eyes open. I’ve met so many men whose lives I would never have otherwise intersected; in the aggregate, it’s enlarged my sense of the possible and my appreciation for human diversity. Mostly, it’s been fun.

Lately, though, I’ve had a different glimpse into the emotional universe of online dating. The luck of the draw brought a large number of missed connections and challenging moments. I felt myself start to slip into that familiar song: Men! What was up with men? But before long, I began to see the other side of the story: the war many men fight between the desire to open their hearts and the terror of being exposed; between wanting to be known and fearing rejection; between showing themselves truly, and wearing a mask that has started to pinch.

I was on the road so much this spring that I over-booked my too-brief times at home. It was like one of those montages in an old movie where the rapid transit of calendar pages symbolizes time’s passage: coffee, walk, drink, coffee, walk drink. At the end of that run, I felt sad, and tried to understand why. Nothing truly terrible had happened; no hearts were broken, no ultimate terrors broke through the barrier between imagination and reality. But I’d been exposed to an intensity of anxiety, loss, and dread—wearing a disguise as bravado or humor, perhaps, but still visible at the seams—and by being over-exposed, I’d absorbed some of it, despite my determination to take it lightly. I realized that it is much better to pace myself, because compressing multiple dates in a short span of time—while maximizing serendipty—also maximizes the potential for missed connections, the potential for tender vulnerability to tip over into brokenness. But I also realized I’d been given a glimpse of the type of challenge that dogs many men.

For instance, within a single week, two men wrote to me, pitching their comments as altruistic, to tell me that the description in my profile of what I am seeking was unattainable. “The person you describe walks a path somewhere between Jascha Heifetz and the Dalai Lama,” wrote one, “and the chances of your finding this person online is statistically insignificant.”

For instance, one man took one look at me and began a monologue about his ex-wife, old girlfriends, and family of origin that lasted for the hour it required to make our way back to the parking lot. Another man tumbled into a premature revelation of intimate information, and then, appalled at the vulnerability he felt, went through an agony of regret. Another man pursued me energetically, broadcasting a lavish commercial for his commitment to emotional honesty, then ran like the wind the first time I took him up on it. Another was so desperately sad—though clearly kind, bright, and persistent despite it—that his sorrow created a sort of black hole no conversation could fill. Another, having obtained my email address, added me to a long recipient list for a series of screeds indicting his friends and family for failing to rescue him from the consequences of a manic episode. He listed his demands: food, shelter, money, sex.

(I also had fun and interesting encounters. I’m slowing down the pace and looking forward to the next—but that’s not my subject today.)

I have to think it was the compression of so many interactions into such a short time that threw so much misery into high relief, because this is not typical of my experience. I’m sure I could cast such stories as comic anecdotes about an off-kilter week in online dating world. But in truth, the intensity of it has made me see something clearly: how easy it is for many men to get lost in gap between desire and vulnerability; how often the opening to possibility is followed by a loud slam of the heart’s door, how often a feeling of exposure leads to a barricade, to regret and self-recrimination at allowing it to be breached.

I didn’t create these responses, but something about my presence triggered them, and I think it is often the same thing, which is my decision not to abide by the old rules, but to be forthright and patient in seeking what I desire. The men who tell me they are performing a public service by explaining that my quest is hopeless have compared themselves to my description of the qualities I am seeking in a partner, and judged themselves so harshly they were compelled to inform me that no man—not just themselves—could measure up. The man whose hour-long monologue insulated him from having to ask me anything about myself sensed some threat to his well-being and erected a wall of words to stave it off. Something about the way I look, perhaps, because he didn’t take time to ask me a single question; indeed, I barely spoke at all. The man who let himself relax into self-revelation with me wanted a response I couldn’t give, and felt betrayed by himself and me because of that. The man who needed to advertise his honesty was clearly expecting that the sizzle alone would sell the steak. I see his point: a good line of patter can sometimes carry you a long way; but perhaps not far enough.

I’m not minimizing the comparable challenges for women who venture forth in online dating world. But when I put myself in the place of these men, I feel the tectonic pressure between a lifelong prime directive to wear the armor and an emergent desire to be seen, known, and loved despite past disappointments. Compassion lubricates the friction of such encounters. I send each man silent blessings, the same ones I send myself and my sisters: may we see and be seen, love and be loved, open our hearts and minds to embrace in the place of fear. May we risk showing up in the service of love.